


Dean's Unfortunate Mistake

by thewinchesterlifestyle



Category: Supernatural
Genre: Accidental Incest, Cunnilingus, F/M, Incest, Loud Sex, Mistaken Identity, Multiple Orgasms, Parent/Child Incest, Rough Sex, Time Travel, Vaginal Fingering, Young Mary Winchester, mommycest
Language: English
Status: Completed
Published: 2017-01-09
Updated: 2017-01-09
Packaged: 2018-09-15 21:17:36
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,904
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9257702
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: He’d been trapped in the past for a week. A whole fucking week and Dean had never hated a monster more than he hated that fucking trickster. It had been a complete accident and he’d never seen it coming.How had a simple hunt gone so fucking wrong?





	

**Author's Note:**

> I had NO IDEA so many of you wanted Mary/Dean (again this is why polls are soooooooooo helpful). Needless to say I figured I'd post this one up. You all really seem to love Dean when he's paired with another Winchester, don't you?
> 
> I decided on a Dean thrown into the past scenario because I have had several on Tumblr mention Dean going back to the past and running into Mary without recognizing her.
> 
> Read the tags though I think knowing the ship should really give you a good idea of what you're in for.
> 
> This is to all of those people who put down Mary/Dean as a ship they would love to see me write and this is honestly a ship I never thought I would write!

He’d been trapped in the past for a week. A whole fucking week and Dean had never hated a monster more than he hated that fucking trickster. It had been a complete accident and he’d never seen it coming. How had a simple hunt gone so fucking wrong?

With a snarl he slammed the blade through the heart of the monster he had been hunting, watching it crumple and die, before he sighed in slight annoyance. At least there were still things to hunt and hunters he’d managed to stumble across in the past. It was safer to have someone at his back on the off chance another hunt went wrong.

“Not bad.” Came a soft voice and Dean glanced over to see Samuel’s daughter, M-something, giving him an appraising look as he flashed a smirk. They had been dancing around each other ever since he’d stumbled across her father on a hunt. Maybe something fun could come out of this unnecessary trip other than killing things. He was more than sure she was just as interested in a night of fun as he was and it never hurt to enjoy a night of good sex with someone that pretty.

Dean stepped closer, let his eyes rove over the gorgeous blonde in front of him, and offered a slight smile when he saw her giving him the very same look. It might be easier than he’d thought and Dean wasn’t about to turn down a free fuck with a gorgeous woman. The slight hesitance from before seemed to have vanished or at least lessened from what it had been.

“I try.” He turned on the charm as easy as breathing and watched interest grow in her bright eyes. It probably helped that he had helped her father and offered to clear out some monsters on his way “out of town”. Dean was thinking about what he needed to say to get her out of her clothes and on her back when she stepped right up to him.

There was no nonsense in her tone, little foreplay and a lot of intent. Just what he liked.

“Let’s get something straight,” she started off and Dean struggled to recall the name he’d heard Samuel say when he’d been only half paying attention ironically because he’d been checking out the older hunter’s daughter. “I’m  _not_  going to get into a relationship with a  _hunter_.” The word was said with a hint of disgust and Dean raised an eyebrow as she continued, “But I have nothing against having a little fun before going our separate ways.”

That was  _exactly_  the kind of thing he was hoping for. A night of no-strings-attached fucking.

“I understand. Your place or my room?”

Her lips quirked and Dean allowed himself to reach out, tugging on soft blonde locks, as she stepped right into his space with a look that had his cock hardening in his pants to an almost painful point. “Your place. I doubt you’d want my Dad to shoot you.”

That would put a damper on his little trip to the past though Dean very much doubted the trickster planned on Dean finding a hot blonde to fuck instead of spending his time worry about getting back to the future.

It was a quick ride to his room and the instant the door shut behind them he stepped right into her space. “You’re gorgeous.” He breathed against her lips, hauling her forward so their bodies were pressed together, before capturing her lips. She tasted sweet as his tongue slid into her mouth and a soft moan reached his ears as his hands wandered over her soft body.

They moved away from the door, kisses and tugging off clothing, until they made it to the bed and Dean let his eyes rove over the black bra and panties hiding the rest of her body from his view. Gorgeous almost didn’t do it and Dean could feel his cock hardening further. He ached to bury himself inside her and fuck until they were both a mess but first he was going to have her writhing under him.

“See something you like?” the tone was teasing and Dean let his eyes slowly drag up her body to look at her face. He took in the flushed cheeks, the kiss swollen lips and the mussed blonde hair.

“Yeah.”

She grinned at him and dragged him in for another kiss, fingers tugging on his boxers and then she was pulling them down. He kicked them to the side, reached out to haul her up and groaned in pleasure when she lifted up, wrapping her legs around his waist, as she pressed against his hard cock.

It was sinful and Dean was more than happy to  _finally_  enjoy something from the past. He’d fucking  _earned_  it.

“I’ll try not to ruin you for any other guy.” Dean grinned when they broke for air and he watched amusement dance in her bright eyes.

* * *

Excitement rushed through her as strong, capable hands moved over her body and wandered down to slide off her panties once she was laid out on the bed. Mary couldn’t bite back the loud moan of approval when Dean immediately parted her legs and started to eat her out. It had pleasure twisting inside of her, warming her belly and her toes curled at the sensation even as she fisted the bed sheets. Dean’s _very_ talented tongue pressed against her clit just right and then he sucked. Her orgasm slammed into her far quicker than she had thought it would and Mary was more than sure anyone in the room over from Dean’s had heard her as she came.

But he didn’t stop.

Fingers slipped into her, pumping and teasing, as Dean continued to tease her clit until another orgasm was building. Her mouth fell open, her cheeks flushed with arousal and her thighs trembled where Dean had hauled them over his shoulders. One hand came up to yank at Dean’s hair before she pushed him closer and her breathing hitched in her throat as her second orgasm of the night rushed through her leaving her limp, panting on the sheets and trying to figure out how much practice he’d had to get that good.

There might not be a future with Dean, she could _never_ marry a hunter, but she had zero problem with enjoying a night having wild, satisfying sex.

He pulled away from her, lips wet and eyes dark, as he moved up and kissed her. Mary didn’t care to taste herself on his lips but as he continued to touch her Mary arched up into the kiss and pressed her body against him. “Condom?” she managed to breathe out, voice raspy and wrecked sounding, as Dean pulled away.

“I prepare for everything.” It was cheeky and she rolled her eyes even as an unwanted kind of fondness filled her. There was something about Dean that made it easy to trust and easy to be around him. A kind of surprising connection that had her offering a one-night-stand instead of waiting for him to hit on her. He moved away and she noticed several condoms. The only thing she could think at the sight of them was _good_ because if he was half as talented in fucking as he was at eating a woman out she was more than interested in multiple rounds. She might as well get everything she could from the experience before he left town or her Dad realized a fellow hunter was fucking his daughter.

She might not want to marry him but she didn’t want him dead.

“Good.” her lips curled as she kept her legs spread and knew what she looked like. More than a few one-night-stands had told her how beautiful she was, how sinful and tempting. Judging by the pure lust in Dean’s eyes and the very impressive, hard cock it was obvious he agreed with her. She reached up to remove her bra while Dean rolled on the condom. With a careless toss she flung it in the direction of a chair and watched with silent satisfaction as his eyes took in her completely naked body.

“You’re gorgeous.”

Pleasure of a different kind lit up inside of her at the obvious tone of awe.

She reached up and hauled him down so he was pressed against her, settled between her legs, as they kissed enthusiastically. His tongue slipped into her mouth, stroking and tasting, as he reached down and she shifted as he pressed inside. Thick and the perfect length of Dean slid inside of her, buried to the hilt, as she rocked up into him. It was a slow, steady rhythm at first, as they broke for air and Mary’s legs hooked around Dean’s hips.

Beneath them the mattress creaked and her breathing started to quicken with each increasingly strong thrust up into her. Mary’s head shoved back into the mattress as pleasure slowly started to build inside her once more and the hard snaps of Dean’s hips started to cause the headboard to rap against the wall in a gradually louder sound. “ _Ohhhh_.” Her eyes rolled and her toes curled as a hand reached between to tease her sensitive clit. “ _Dean. Dean._ ”

It was almost getting to the point of too much as his hand fell away and Dean resumed fucking up into her. He felt hot and heavy, pressing her down into the mattress, as the only thing Mary could do was tighten her thighs around his hips and grip onto warm, sweat damp skin as he started to pound into her. Dean fucked her like he knew exactly how to take care of a woman and her inner muscles started to flutter around him as her third orgasm was slowly dragged out of her.

“ _Fuck_ ,” he hissed it against her overwarm skin, body still thrusting up into her, while her moans only got louder and louder as his name became a breathless mantra the closer she came. Dean’s own moans echoed in the room as he moved quicker, chasing his own release, and the headboard had started to bang against the wall loudly. “You feel so good. So fucking hot.”

“Yes.” She moaned when he touched her again, “There yes please yes yes yes. _Dean!_ ”

Mary’s third orgasm left her practically whimpering at the sensation as Dean fucked her through it, grunting with each thrust, until his pace fell off and he slammed up into her, hips jerking and breathing quickening, as he came with a deep moan of satisfaction. He stayed there, coming down from the high of his own orgasm, before slowly withdrawing and leaving her laid out on the bed panting.

She could hear him moving around, knew he was tossing the condom and cleaning up, before the bed dipped and he was back. “Give me a bit and we’ll try a different position.” There was a brief pause as knowing fingers trailed over her shaking body, “That is…if you’re interested in spending the night?”

As if that was even a question?

Mary turned her head and with surprising energy she straddled him, body pressed right over his now soft cock, as she stared down at him and knew the flush from her cheeks was slowly fading as she came down from her high of pleasure. “I have nowhere else to be.” Because she didn’t and how could she pass up amazing sex?

They kissed, teasing and pressed together, until Mary could feel Dean hardening once more. She grinned at him, knew it looked wicked, as her fingers curled over his hardening cock and she teasingly stroked him until he was thrusting against her hand while releasing encouraging moans.

This time she let him maneuver her so she was on her spread out knees, ass raised and upper body lowered to the mattress. It wasn’t a position she often found herself in but as Dean rubbed against her clit and finger fucked her Mary was more than willing to remain in the position he’d guided her into. If they made it to a third round she was going to shove him down and ride him until he was moaning her name.

When she was wet, practically begging him to push inside, Dean’s fingers moved away and the mattress groaned as he shifted. Her mouth fell open as inch by inch Dean sunk into her wet heat, stuffing her full and gripping her hips as he moaned deeply in appreciation. “ _Fuck_.” He breathed out in that wrecked tone, “You’re fucking perfect.”

Mary started to reply but Dean had already rolled his hips back and snapped them forward with a loud smack as he buried himself balls deep inside of her once more. The pace didn’t start off near as slow and teasing as it had when she was on her back. This time it was more of a dirty, hard fuck that left her breathless and her blood practically singing. She could hear the loud slap of skin against skin over the knock of the headboard and their shared moans as he fucked them both towards their orgasms.

Her fingers dug into the sheets and her eyes slipped closed as Dean pounded into her from behind.

They spent the night touching, tasting and fucking. She almost felt sorry for the person in the room over who had pounded on the wall several times demanding that they _keep it the fuck down_ but it was a bit impossible to feel sorry when it felt so deliciously good. When they fell asleep Mary was sure it would be better to slip out of the room instead of staying after but she was too perfectly fucked out to do much of anything other than slip off into unconsciousness.

In the morning she woke alone, no trace that Dean had been there other than the loose-limbed feeling of satisfaction from a night of good sex, as she looked around trying to find some sign that he’d left a note about his whereabouts. She couldn’t. There wasn’t a trace of Dean left in town.

* * *

“ _Oh Dean._ _Shame on you_ ,” The trickster grinned wickedly at him, “ _You naughty, naughty boy_.”

Dean stood before the trickster, back in his own time and half-asleep after a night of wild sex, as he blinked in confusion trying to figure out what the annoyance in front of him could possibly be alluding to. “What? Where?” he glanced around trying to figure out what was going on as the look on the trickster’s face only seemed to get more wicked.

Something similar to dread started to fill him as the silence stretched on between them and the level of smugness in the trickster only increased.

“I always knew you were a Momma’s Boy but never in my wildest dreams would I have imagined that you were _that kind_ of Momma’s Boy.” Dean’s heart stopped and horror started to fill him, “Did she taste as good as those apple pies she used to give you? Was being buried inside of her as good as one of those hugs you still cherish so much?”

Dean stumbled back, denial screaming in his mind, as his stomach twisted and Dean turned to the side only to get sick. He heaved and choked, disgusted and horrified, as the words echoed inside of his mind. Every single thing he’d done with who he now knew was his _Mom_ replayed in his mind like a dark, twisted nightmare that would never end. Eating her out, twisting his fingers inside of her while she moaned and then fucking her. On her back, with her ass raised and then with her riding him hard, fully breasts bouncing with each rock of her hips and curly blonde hair wild as she moved.

“You’re lying.” His voice was rough and he hated the taste in his mouth but it was far better than remembering the taste of his _Mom_ on his tongue after he’d eaten her out.

“Dean. Why would I lie when the truth is far more interesting?” the trickster laughed at him and Dean had never wanted to kill something so badly in his entire life, “I sent you back there for fun. I never would have imagined getting this kind of enjoyment out of it. Do you think if I sent Sammy back he might find his way between your Mom’s thighs? Or would he manage to resist temptation?”

Dean snarled, “I’ll fucking kill you. I’ll wipe you from existence.” His fingers itched for a weapon and his mind screamed for revenge. This could never be forgiven. His memories of his Mom had been tainted, _ruined_ , and nothing short of memory loss would remove that horrible reality from his mind. He could never look at Sam without knowing what he’d done with their Mom. How had he not realized? It was all more than obvious who she had been now that he was looking back on it with knowledge.

“Good luck with that, Dean-o.”

And then the trickster was gone with a laugh. Just as quick as the trickster had left Dean’s anger collapsed on itself and the horror of his actions slammed into him causing him to crash to his knees with a sound of emotional agony. He’d fucked his own Mom and he could still hear her moaning his name in pleasure.

**Author's Note:**

> So did any of those who wanted Mary/Dean enjoy my first attempt at the ship?


End file.
